Why Should Successful Founders Mentor New Startups? "We Have an Obligation to Help Fellow Travelers"

A startup founder recently asked me a simple, yet startling, question during our monthly meetings. We have been working together for nearly two years, and as with all startups she has had her ups and downs. We have had all manner of conversations over the years and yet, in this one instance, her simple question floored me - "When I asked if you would be my mentor, why did you say yes?"

The first thing that surprised me was that she said "mentor" and not "adviser". I have the pleasure of advising many companies. This means that I meet with them every now and again to offer some thoughts on a discrete problem, or I make an introduction or two. However, my relationship here was different. I was more than an adviser. I was a mentor to her. We meet once a month and I know a tremendous amount about her business, where she has been and where she hopes to go. I am proud to be her mentor so I wanted to provide an honest answer.

After collecting myself, I explained that there were three reasons why I said yes‎, in no particular order of importance:

1. She was the first to ask.
2. Mentoring helps reinforce the lessons I'm learning at my own company.
3. I believe we have an obligation to help fellow travelers.

Many of the students I have taught over the years will email and ask if they can discuss their businesses. I am always happy to help, so‎ I'll meet with them and offer candid feedback on their ideas. These aspiring founders frequently end our time together by asking to return when their plans have progressed. I would always say yes, but few have ever returned. Some never make any progress; some don't like the very direct feedback I am prone to give; some presumably just forget to follow up. So when asked why I agreed to mentor her, part of the answer was simply that she asked. I had time and she asked, so I said yes. If someone had asked before her, then I really would not have had the time.

2. Mentoring Helps Reinforce The Lessons I am Learning at My Own Company. 

I have learned a great many things on my entrepreneurial journey at Work Market: mistakes I hopefully won't repeat, important lessons to refer back to and valuable insights from colleagues. Mentoring this founder and hearing about her own struggles and breakthroughs has forced me to reflect on when we were at a similar stage as a company. Offering her advice and describing the opportunities we missed (we all miss many) helps to codify these hard-won lessons and prepares me for my next adventure.

3. We Have An Obligation To Help Fellow Travelers. 

I have walked this tumultuous, crazy, startup path three times. It's one of the hardest ‎journeys you will ever take. It will test limits you never knew you had and then demand you to push beyond them. So, when the journey ends, regardless of the outcome, you have gained invaluable experience. Pass it along. I can promise you this: whatever outcome you had, you didn't get there alone. You had co-founders, colleagues, investors, mentors, advisers, customers, and of course friends and family that all helped in sometimes small, but many times, immeasurable ways. You owe it to them, as well as to yourself, to help others who are embarking upon that similar difficult path. No one can make it alone.

If you have made it to the end of a startup journey, and if you have the time, stretch out your hand and help the next traveler. They will be grateful and you will greatly benefit as well.